4Q9Z

Human Protein Kinase C Theta in Complex with Compound35 ((1R)-9-(AZETIDIN-3-YLAMINO)-1,8-DIMETHYL-3,5-DIHYDRO[1,2,4]TRIAZINO[3,4-C][1,4]BENZOXAZIN-2(1H)-ONE)


Experimental Data Snapshot

  • Method: X-RAY DIFFRACTION
  • Resolution: 2.60 Å
  • R-Value Free: 0.256 
  • R-Value Work: 0.219 
  • R-Value Observed: 0.220 

wwPDB Validation   3D Report Full Report


Ligand Structure Quality Assessment 


This is version 1.3 of the entry. See complete history


Literature

Discovery of Selective and Orally Bioavailable Protein Kinase C theta (PKC theta ) Inhibitors from a Fragment Hit.

George, D.M.Breinlinger, E.C.Friedman, M.Zhang, Y.Wang, J.Argiriadi, M.Bansal-Pakala, P.Barth, M.Duignan, D.B.Honore, P.Lang, Q.Mittelstadt, S.Potin, D.Rundell, L.Edmunds, J.J.

(2015) J Med Chem 58: 222-236

  • DOI: https://doi.org/10.1021/jm500669m
  • Primary Citation of Related Structures:  
    4Q9S, 4Q9Z

  • PubMed Abstract: 

    Protein kinase Cθ (PKCθ) regulates a key step in the activation of T cells. On the basis of its mechanism of action, inhibition of this kinase is hypothesized to serve as an effective therapy for autoimmune diseases such as rheumatoid arthritis (RA), inflammatory bowel disease (IBD), and psoriasis. Herein, the discovery of a small molecule PKCθ inhibitor is described, starting from a fragment hit 1 and advancing to compound 41 through the use of structure-based drug design. Compound 41 demonstrates excellent in vitro activity, good oral pharmacokinetics, and efficacy in both an acute in vivo mechanistic model and a chronic in vivo disease model but suffers from tolerability issues upon chronic dosing.


  • Organizational Affiliation

    AbbVie Bioresearch Center , 381 Plantation Street, Worcester, Massachusetts 01605, United States.


Macromolecules
Find similar proteins by:  (by identity cutoff)  |  3D Structure
Entity ID: 1
MoleculeChains Sequence LengthOrganismDetailsImage
HUMAN PROTEIN KINASE C THETA
A, B
334Homo sapiensMutation(s): 2 
Gene Names: PRKCQPRKCT
EC: 2.7.11.13
UniProt & NIH Common Fund Data Resources
Find proteins for Q04759 (Homo sapiens)
Explore Q04759 
Go to UniProtKB:  Q04759
PHAROS:  Q04759
GTEx:  ENSG00000065675 
Entity Groups  
Sequence Clusters30% Identity50% Identity70% Identity90% Identity95% Identity100% Identity
UniProt GroupQ04759
Sequence Annotations
Expand
  • Reference Sequence
Small Molecules
Ligands 2 Unique
IDChains Name / Formula / InChI Key2D Diagram3D Interactions
PZW
Query on PZW

Download Ideal Coordinates CCD File 
C [auth A],
E [auth B]
(1R)-9-(azetidin-3-ylamino)-1,8-dimethyl-3,5-dihydro[1,2,4]triazino[3,4-c][1,4]benzoxazin-2(1H)-one
C15 H19 N5 O2
YWULJUISHNTGOC-SECBINFHSA-N
NA
Query on NA

Download Ideal Coordinates CCD File 
D [auth A]SODIUM ION
Na
FKNQFGJONOIPTF-UHFFFAOYSA-N
Modified Residues  1 Unique
IDChains TypeFormula2D DiagramParent
SEP
Query on SEP
A, B
L-PEPTIDE LINKINGC3 H8 N O6 PSER
Binding Affinity Annotations 
IDSourceBinding Affinity
PZW BindingDB:  4Q9Z IC50: min: 55, max: 110 (nM) from 2 assay(s)
Experimental Data & Validation

Experimental Data

  • Method: X-RAY DIFFRACTION
  • Resolution: 2.60 Å
  • R-Value Free: 0.256 
  • R-Value Work: 0.219 
  • R-Value Observed: 0.220 
  • Space Group: P 21 21 21
Unit Cell:
Length ( Å )Angle ( ˚ )
a = 76.954α = 90
b = 78.575β = 90
c = 146.966γ = 90
Software Package:
Software NamePurpose
REFMACrefinement
XDSdata reduction
XSCALEdata scaling

Structure Validation

View Full Validation Report



Ligand Structure Quality Assessment 


Entry History 

Deposition Data

Revision History  (Full details and data files)

  • Version 1.0: 2014-07-02
    Type: Initial release
  • Version 1.1: 2014-07-30
    Changes: Database references
  • Version 1.2: 2014-09-17
    Changes: Source and taxonomy
  • Version 1.3: 2015-01-21
    Changes: Database references